Cyclohexanecarboxaldehyde → HCID 57257056, compound

Participants

Reaction Steps

5-(Adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c, d with the modification that cyclohept-4-enecarboxaldehyde (D. F. Murray et al. J. Org Chem. 1986, 51, 1) was used in step d instead of cyclohexanecarboxaldehyde. The benzyl ester was hydrolysed according to the procedure of Example 211, step b and the resulting 5-(adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carboxylic acid was reacted with 3-amino-benzoic acid methyl ester according to the procedure of Example 20, step d to afford 3-{[5-(adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carbonyl]-amino}-benzoic acid methyl ester. The methyl ester was hydrolysed according to the procedure of Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.90 (1H, br s), 12.40 (1H, br s), 9.87 (1H, br s), 8.44 (1H, s), 7.93 (1H, d), 7.63 (1H, d), 7.42 (1H, t), 5.81 (2H, m), 4.79 (2H, s), 3.04 (1H, m), 2.30 (2H, m), 2.11 (5H, m), 1.96 (2H, m), 1.76-1.53 (14H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 59.69; H, 7.90; N, 7.88%. C36H52N4O9.2.1 mols H2O requires: C, 59.81; H, 7.84; N, 7.75%.

Provenance & Evidence